Manhattan's Elite
by JensensGurl07
Summary: Brooke used to date Dean Winchester, and now is with Julian Baker. Other couples in my story Chuck/Blair Sam/Peyton. Brooke is the main character. One Tree Hill/Gossip Girl/Supernatural crossover.
1. Chapter 1

**Manhattan's Elite**

It was a normal day in The Upper East Side. Blair Waldorf was waiting in the lobby of The Palace for her best friend, Brooke Bass and her boyfriend, Chuck Bass. It was Chuck's 18th birthday and they were all heading to Butter for his birthday, which their friend Nate Archibald had bought out for the night.

"Finally!! I've been waiting down here forever!" Blair yelled when she saw Brooke and Chuck heading down the stairs to the lobby.

"It wasn't forever, just 20 minutes. You need to learn some patience." Brooke laughed, as she hugged her best friend.

"Blair learn some patience? Not in this lifetime." Chuck joked.

"Hahaha you Bass siblings are hilarious, ganging up on me. Just you wait one of these days I'll get you back." Blair laughed.

"Oh come on B! We only tease you because we love you."

"Speak for yourself, Brooke!" Chuck said, winking at Blair.

"Eww, ok can you two love birds wait until were at the bar, and I'm not around, please?"

"Sorry sis, don't think that can happen." Chuck joked, grabbing Blair's hand then kissed her again.

"Seriously I will stay here and drink!" Brooke warned.

"Chuck have some compassion toward your sister, especially since Julian just left." Julian Baker was Brooke's boyfriend who left to go back to LA after his movie didn't work out. Ever since he left Brooke hasn't been able to leave the house. Today was the first day that everyone finally convinced her to go out."

"You promised you wouldn't say that name tonight!"

"I'm sorry, I didn't mean --"

"Blair, stop before you make it worse. You can't take it back now." Chuck cut her off.

"It's fine. She forgot!"

"I'm just worried about you! I don't want you to stay locked in your room for another couple weeks over him. I swear he better not come back here, or he and my fist will be talking."

"I know thanks, but I don't think you have to worry about him coming back; he said he wasn't."

"That's even worse telling you he's not coming back as he's leaving."

"He didn't tell me when he left."

"Then when?!"

"Last night when I called him."

"And you did that why?"

"Because it was his birthday Chuck, and I needed to hear his voice, happy?"

Chuck was about to say something when Blair stepped in front of him and whispered, "Stop, leave her alone. If she wanted to hear his voice one more time and hear it from him that he wasn't coming back then fine. Just let it go now, your just going to cause her more pain then she needs right now. It's supposed to be a fun night."

"Fine, let's go. Nate's probably looking for us."

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Everyone was now at the party, so everyone started drinking and dancing after they had all wished Chuck a "happy birthday."

"Nate, do you even know all of these people?" Brooke asked when people kept showing up that they didn't know.

"No." He answered, when he looked around. "Someone must have found out about the party and wrote it on **Gossip Girl**."

"Great! We got to watch our every move now." Brooke laughed.

"How are you doing Brooke since he left?" Nate wondered.

"It's tough, I won't lie to you. But I will get by it, I have to since he's not coming back."

"You don't know that."

"Yeah, I do. I called him last night to wish him a happy birthday and the he told me he wasn't coming back and move on and not call him again."

"He's lying. He loves you and he wants to be with you, he's just hurting too. You can tell how much he loves you by the way he is when he is with you. Just have some faith Brooke."

"I won't be able to move on for awhile, and by the time I do if he still hasn't come back then I will know my answer."

"Yeah. I'm sorry your hurting Brooke."

"Thanks Nate, but its ok. Don't worry about me I'm tough. Enjoy the party. I'm going to get a drink." She said, hugging him and heading to the bar.

"What can I get you Ms. Bass?" The bartender asked her.

"Vodka tonic, please." She smiled at the bartender.

"Here you go. Enjoy yourself Ms. Bass." The bartender handed her, her drink and then she headed for the dance floor.

Blair came up behind her, "Hey Brooke, you got me a drink, thanks." She said, as she took the drink from Brooke and ran off laughing.

"Your dead, Blair!" She laughed after her.

"And why do you always let her do that to you?" A voice from behind her stated, which caused her to turn around to face who the voice belonged too, it was exactly who she thought it was, his voice hasn't changed since the last time she saw him.


	2. Chapter 2

**Chapter 2**

"Dean Winchester." She said as she faced him. "What brings you back to town?"

"Well I read on **Gossip Girl** that their was a party, had to come back." He smiled.

"You've got to be kidding me. I know your lying, your not good at lying to me, you never were."

"I can't tell you why I'm here."

"You can't or you won't? There's a difference."

"I want to but Sam will kill me if I told you."

"Sam's here too?? Peyton must have him on a short leash." Brooke said, which made Dean laugh.

"Where is your boytoy? I thought you'd have him on a 'short leash' as you call it."

"I should, especailly since you."

"That's not fair."

"And it was fair for me to find out that you had cheated on me with Peyton? What does all the Winchester brothers see in her anyway? Guess I'll always be second best against her!"

"I thought we got passed this!"

"Well you thought wrong. And she keeps her men on a short leash, because she knows how easy men will turn on you; she would know best."

"So you never answered my question!" He changed the subject.

"Which was?"

"Where's Julian?"

"He's gone! We broke up, but you knew that if you were reading **Gossip Girl**, which I don't think you did. Sam told you about the party, didn't he?"

"Yeah he did. I'm sorry about Julian, though."

"I don't need to hear that, at least not from you."

"Brooke, please. I just want to get past this. I don't know how many times I need to say I'm sorry. I wish there was something I can do."

"I don't think we can. Dean, I didn't just lose my boyfriend that day but I lost my best friend. And there is nothing you can do, just leave me alone."

"I'm really sorry, Brooke. I never wanted this to happen." He responded as he put his hand on her shoulder, which she removed right away.

"Don't touch me, Dean not now or ever again." She said walking away.

"Brooke!" He called after her, following her.

"Dean, just leave her alone." Sam said, blocking him.

"Sam I just need to explain t--"

"Dean she doesn't want to hear it. I told you that you coming wasn't a good idea. But then again, when do you ever listen to a word I say?"

Dean started walking away.

"Where are you going?"

"Out! I need some fresh air."

"Dean." Sam said, holding him back.

"Sam, just let me go. You said it yourself, I shouldn't have come so now I'm leaving."

"You can't just walk away when you can't deal with what's going on!"

"Watch me, Sam." Dean answered, walking away. Sam stood in front of him again. "Get away from me Sam."

"No."

"Suit yourself." Dean said punching him in the face and left as everyone watched.

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Peyton came to Sam's side in a flash.

"Are you ok?"

"Yeah, I'm fine Pey. He's just mad that's all. And he lashes out, when he's mad. You know that."

"Yeah, but he's blaming you and it's not yur fault!"

"I was right and he was wrong and he never likes that."

"Did you want to go after him?"

"No I'll just let him cool down."

"Ok, let's go get a drink then."

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"Brooke are you ok?" Blair said, sitting beside her.

"Yeah, I'm fine. Seeing Dean was the last thing I needed today."

"I bet. He left though, so let's go have some fun. Chucks at the bar. I told him I would talk to you."

"SureI need a drink bad now." Brooke laughed, heading to the bar with Blair.

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Dean was walking outside, cooling down when he spotted a Pharmacy. He remembered that he still had a prescription for a refill on some anti-depressants that the doctor gave him. He went inside to the counter and gave the cashier the prescription, and waited as they got it ready.

"Here you go. You have to take one tablet twice a day and never with alcohol; preferrably with food, but it's okif you have it on an empty stomach." he explained as he handed the pills to Dean.

"Thanks." Dean answered taking the pills from him and left.

When he got outside he took one right away then headed back to his car; he decided to call it a night, he didn't want to go back to the party, didn't want to deal with anyone especailly Sam.

**Gossip Girl here. Looks like the party was full of surprises one being, seeing the older Winchester make his grand entrance at the party. He was seen with his ex . Got bets saying that they will be back together by the end of the week. Brooke never stays single for long, you got yourself to blame Julian. You know you love me xoxo Gossip Girl**


	3. Chapter 3

**Chapter 3**

"Brooke get up!" Blair screamed in the morning.

"Talk quiet please." Brooke answered, holding her pounding head.

"Trust me once you read what **Gossip Girl** wrote it will kill your hangover."

"I don't think I want to know." She announced, pulling her pillow over her head.

Blair just took it off her head, "Yes you do!"

"Fine." She said getting out of bed and headed to her already open computer, and started reading the entry. "What??" Brooke said when she finished reading it. "Someone took a picture of me and Dean and suddenly that means were getting back together?"

"I want to know who sent that photo to **Gossip Girl**." Blair recalled.

"That's what I want to know." Chuck responded from the doorway. "I just saw it and wanted to see how you reacted to it."

"I'm fine Chuck, thanks."

"Ok, I'm going to get ready for school."

"Yeah, I should probably start getting ready to head to the store soon." Brooke said, when Chuck headed back to his room.

"If anyone says anything about you, I will kick their ass for you." Blair winked, as she headed to the door, "I will wait for Chuck downstairs."

"Ok, I will catch up with you two later."

"Rise and shine, Sammy!" Dean yelled at his brother.

"What?? Why?"

"I have to get out of town, Sam. Just want to know whether or not your coming."

"Dean you can't run away!"

"I'm not. I think I found a lead on Lillith!"

"I want in, you know that; but I can't leave I just got here, and Peyton planned this whole day just me and her. I can't bail."

"Of course you can you just choose not too!" Dean said, throwing his clothes in his bag.

"Dean you can't take on Lillith by yourself. You need me just wait a couple of days."

"She will be gone by then. Sam look how long it took us to find her!"

"Dean please. I'm sure Ru—"

"Ruby never helps us find her Sam, because she knows she will kill her as well.

"What about Castiel?"

"What about him? Last time we saw him he said that he didn't serve humans remember?" Dean pointed out, "This is the only way."

A knock on the door broke the silence between them. Dean pulled his bag over his shoulder and opened the door.

"Well, look what the cat dragged in. You heard your name didn't you Ruby?"

"Yes, but I was on my way here anyway. You got a big target on your back Sam and if your not ready for it, you could lose." She said coming in and sitting on the bed.

"A target? What target?!" Sam questioned.

"Lillith! She's on her way over here now, I had to warn you!"

Brooke ended up just staying at home. She hadn't been sleeping well since Julian left, so she thought she would catch some more rest while she could. Just as she was about to fall asleep her cell phone rand, she answered it without looking at the called ID.

"Hello?" She yawned in the phone.

"Did I wake you?" The other voice on the phone responded; which she recognized right away, waking her up.

"No of course not. I was just trying to get over this hangover."

"Yeah, I read all about the party this morning on **Gossip Girl**."

"Julian, let me explain--"

"Brooke I didn't call because of the posting. I wouldn't blame you if you did anyway. And I don't care about what did or didn't happen."

"Then why did you call then?"

"Look out your window."

"Ok." She answered getting out of bed and heading to her window. When she got there she saw Julian standing in front of the Palace holding a bouquet of roses, "Wha--? I thought you said you weren't coming back?"

"That's what I said! Doesn't mean I actually meant it." He smiled as she left her window she sat back down on her bed. "I'm sorry, I thought if I said the words out loud that I could believe them. Just like when I told you I didn't love you anymore. But that doesn't change what I feel in my heart, and it never will. I love you Brooke Bass and nothing will change that, I know that now."

Brooke was silent on the other end of the phone, but he could hear that she was crying. "I'm sorry I hurt you." He said starting to walk back to where he left his car when he heard the door of the Palace open. He turned around to see Brooke standing there wearing shorts and a tank top, looking at him and holding in her tears that were forming. They both looked at eachother then Brooke ran up to him and kissed him.

"I love you too Julian Baker."

**Gossip Girl here. Looks like Julian couldn't stay away for long. Meanwhile, back at the Winchesters motel there was a mysterious blonde heading in the room. Better decide on who you want B. You know you love me xoxo Gossip Girl**


	4. Chapter 4

**Chapter 4**

Blair got the new **Gossip Girl** post that was sent to her phone and called Brooke right away. The phone rang a couple of times before Brooke answered.

"Blair, whats up?"

"Is it true?"

"What are you talking about?" She asked confused.

"Julian! Did he come back?"

"Oh.. that, yeah he did."

"And you didn't at least text me to let me know."

"I'm sorry Blair! I was going to, but then I kept thinking that this was a dream that I was going to wake up from soon."

"Well as soon as I'm done my last class I'm heading over with Chuck. I would come now but I have an in-class exam, so I can't miss that."

"Alright I will see you guys soon then."

"Bye." Blair said and hung up.

"Who was that?" Julian asked when he came back in the room.

"Blair. **Gossip Girl** is right on top of your arrival. Guess I'm not dreaming after all."

"No, baby your not. And this time I'm not going anywhere. I shouldn't have left the first time, I realized that as soon I stepped on the plane." Julian came closer to her and kissed her.

"I should have came with you."

"No I shouldn't have given you that decision. You came to New York to stay with Chuck after your parents died, because he's the only family you have left. I shouldn't have made you decide between us, of course you would pick your family. I would too—if I were you. I'm sorry."

"Julian, it's ok. I forgive you." She smiled at him as her phone went off.

"Blair again?" Julian laughed.

"Yeah, she said Chuck wants me to buy some more scotch."

"I'll come with you!!"

"No it's ok, no need it's just a block away. I'll take the limo, I won't be more than 5 minutes." She said as she grabbed her purse, and kissed him. "Unpack or something while I'm gone."

"What does Lillith want with me?!" Sam asked.

"What does she always want, Sam? You dead, Dean too. And is she knows about Peyton, she's dead as well!" Ruby answered. "I don't get how she found you guys anyway. You still have my hex bags don't you?!"

Dean and Sam looked over at eachother, but neither of them said anything.

"You two chuckleheads lost my hex bags didn't you?!"

"We didn't lose it, we just misplace them." Dean stated.

"That's right you guys. You had one job and you failed!"

"Well Dean was going to go after her, guess you didn't need to leave anymore, huh!" Sam smiled.

"I will leave once Lillith is dead. I'm not going to stay in a town that I'm not wanted." Dean answered, throwing his bag back on his bed.

"Dean, I need to talk to Sam about something, can you excuse us for a couple minutes?" Ruby asked.

"Sure, I was going to grab a drink anyway. I will see you later!" Dean said leaving.

"Do you need more? You know if your going to kill Lillith you will need a lot more than you have now." Ruby told him.

"I know I do, I almost feel strong enough, to destroy her for good." Sam answered, grabbing his knife. "You ready?"

Dean drove to Main St. and got out of his car, then he leaned against his car for a couple minutes and took out his bottle of pills, took two out and swallowed it.

"What are you doing here?" A familiar voice said from his side, which caused him to throw the pills behind his back and face her.

"Brooke! I was just heading to the bar for a few beers."

"What are you holding?" She said noticing his hands were behind his back and he was a little more nervous around her, then he normally is.

"Nothing." He answered.

"It's something, or you wouldn't look this nervous."

"I'm not nervous!" He lied.

"Show me."

"I can't!"

"Sure you just don't want to!"

"True"

"Fine, I will just have to take it from you." She said, pulling at his arm that was behind his back.

"Brooke, stop it!" He broadcasted as he lost grip of his pills and they fell to the ground with a big clank. He bent down to grab it before Brooke, but it was too last, she got them.

"Dean what is this?" She said as she looked at the bottle then back to Dean, waiting for an answer.

"If you must know—It's anti-depressants."

"You must have had them a long time, it's half empty."

"No, I got this one the day of Chuck's birthday, after I left the party."

"And you've had all these pills in a matter of 2 days?!"

"Not like its your business but yes. I've been kinda stressed and depressed lately. It's no big deal." Dean answered, grabbing his pills back and shoved them back in his pocket.

"It is a big deal! Does Sam know your popping pills?"

"No and he's not going to find out."

"He has a right to know Dean, he's your brother! Either you tell him or I will."

"Brooke, that's not fair. There is something going on with Sam too and he's not telling me anything. Once he opens up then I will too, until then let it go, Bass!"

"Then stop taking those pills! Please before you get addicted."

"Why don't you just go, please. It's like you care whether or not I—"

"Don't finish that sentence Dean. You know I care about you and what happens to you. Last year when you disappeared for 6 months I thought you were dead and Sam never took any of my calls."

"Sam didn't tell me that. He told me that you moved on."

"With who?"

"I don't know Julian?"

"That's impossible because I didn't meet Julian until a year after you disappeared."

"I'm so sorry. I wanted to tell you what was happening, but I couldn't without having you in danger, and that's something I didn't want to happen."

"So that's why you made sure I walked in on you and Peyton right before you disappeared?"

"Yes, I'm sorry. I didn't want you around and I didn't care about Peyton and what happened to her. That sounds mean, but I would rather have her in danger than you. And I never cheated on you Brooke, we just made it look like I did and I'm sorry for hurting you. That was the last thing I wanted to do." Dean broadcasted, as Brooke started tearing up.

"Dean don't say that!"

"What did I say?"

"That you never slept with her. I knew there was something you were hiding when I caught you guys in bed, but I convinced myself to hate you both, and now your telling me I was right? Sam told me that I was crazy to think that!" She announced as a tear fell from her eye.

"Don't cry Brooke, please. I never wanted to see you in this much pain, and I never wanted to be the one that made you be in this much pain." He answered wiping the tears from her eyes, and the pulled her close for a hug, which to his surprise she didn't push away from.

"Well, never expected Dean Winchester to be found in this part of town." A voice behind them stated, causing Dean to break out of the hug and step in front of Brooke.

**Guess Brooke couldn't stay away from the older Winchester for very long. They were spotted in front of the liquor, getting kinda cozy. Keep me updated guys. You know you love me, xoxo Gossip Girl**


	5. Chapter 5

**Chapter 5**

"So what brings you to New York, Dean?" The voice questioned, as he took a step closer to Dean who stood protectivley infront of Brooke.

"Passing through." He lied.

"Really I find that hard to believe. Wouldn't you be gone by now if that were true."

"I packed this morning, just came for one last beer before I leave this place for good. I've been in this town a couple days and was here years before. And there is nothing in this town that would keep me here, or that want me here now. " Dean stated.

"That's too bad, thought we could catch up. Have a few drinks like the good old days."

"I will take a raincheck on that."

"Of course." The man said, finally seeing Brooke's face hiding behind Dean. "Well Dean, you sure do have the best taste in women." He smiled up at Brooke and extended his hand. "I'm Gordon Walker."

Julian was unpacking when Chuck and Blair got to the Palace. They went upstairs to Brooke's room but only saw Julian.

"Where's Brooke?" Chuck asked when he stepped inside the room.

"She went to buy you more scotch and insisted on going alone. She will be back soon."

"Are you staying for sure this time or are you going to leave in a couple days and break her heart even more than you already have?!"

"Chuck!" Blair yelled.

"It's ok Blair, he's only looking out for his sister, just like Brooke does for him. That's what families do for eachother—or what they are supposed to do."

"That's not an answer, Baker!"

"I'm here for good. I never want to leave her again. It hurt too much to be away from fer for that long."

"Good, because if you hurt her again I will kill you, that's a promise!"

"Ok, fair enough. You warned me so I only have myself to blame if it comes to that."

"Don't be a smart-ass!"

"Ok Chuck stop." Blair told him.

"I'm sorry. I'm going to wait for Brooke in the living room." Chuck said, leaving the room and heading downstairs.

"Don't listen to him Julian." She announced when Chuck left.

"You don't have to explain for him, Blair. I get it." Julian told her before she left and joined Chuck downstairs.

"Stay away from her, Gordon!" Dean said, pushing Gordon's hand away.

"What's the matter, Dean? Don't want me around her, do you?"

"What do you want Gordon?" Dean asked when Gordon's phone rang.

"Hold that thought." He stated as he answered his phone.

"Dean what's going on?" Brooke whispered. "Why do you want Gordon to stay away from me?"

"He is not a nice person, and he wants Sam dead. Just stay behind me."

"Fine." She agreed as Gordon hung up the phone.

"How is Sam doing?" Gordon asked as he started walking toward them again.

"He's fine. Why do you care?!"

"I don't"

"What do you want then?"

"Just want to get to know the girl your hiding, you know Brooke Bass!" He smiled as he looked over at Brooke.

"How do you know my name?" She asked, scared at the way Gordon was looking at her!

"Gordon, what the hell do you want!" Dean yelled getting upset.

"Calm down, Dean. Why don't you take some more pills." He laughed.

"You think this is funny what your doing? Messing with everyone's lives!"

"Not everyone's –just yours."

"Son of a bitch!" Dean yelled as he punched him in the face.

"Your going to regret that!" Gordon said punching his back, hard enough that he fellto the ground. When Dean got back up, Gordon had grabbed Brooke's arm and pulled her closer to him, pulling out his knife and putting it to her throat.

"Whoa Gordon. She hasn't done anything to you."

"I know but obviously you care a lot about her, so I have to use her to get you to do anything I want. You do what I say and your precious Brooke won't get hurt, alright?"

"Fine. I will do anything."

"Thought you would say that." Gordon smirked.

"Then what do you want?!"

"I don't like your attitude Mr. Winchester. Do I have to show you what's at stake here?!" He questioned putting the knife closer to Brooke's throat; which make Brooke wince in pain.

"No, ok I'm sorry. Gordon, just let her go!"

"That won't work. Look our ride is here." He said as a limo pulled up, and walked toward it with Brooke.

"Grodon what do you want? Leave her alone, she has nothing to do this." Dean said walking in front of Brooke.

"I will call you with what I want later! But it's kind of easy if you think about it."

"He wants money, Dean." Brooke answered.

"She's smart. No wonder why you didn't what to risk anything happening to her. She's a keeper that's for sure."

"How much money do you want?"

"Well she's loaded – her dad was anyway with Bass industries, which is worth more than a billion dollars, so I'm just going to ask for 21 million."

"Twenty-one million?! Wha--! How do you expect me to get that!"

"You'll find a way. Especially if you want to see her alive again."

"Dean call Chuck, he will give you the money!" Brooke stated as Gordon pushed her in the limo.

"You have 24 hours Dean!" He said, getting into the limo and told the driver to take off.

"Son of a bitch!" Dean yelled when they drove away.

"Do you talk to yourself often?" Blair asked, coming up behind him, causing Dean to turn around and face her.

"Blair what are you doing here?" He said looking around.

"Where's Brooke?"

"Lets hope your brother comes through for you." Gordon said placing his arm on Brooke's houlder, only to get her to push it off.

"Don't touch me!"

"Feisty aren't you?"

"Just don't hurt anyone I care about. Especailly—"

"Your brother Chuck? Or your boyfriend Julian?" He cut her off.

"How do you know so much about me? Who are you?"

"I'm a very good hunter!"

"A hunter?!" She said confused.

"I will explain more later. While we wait for Dean."

"Don't hurt anyone else, please."

"But I can't hurt out. Your just playing it off like I can."

"What?"

"I know that your pregnant Brooke, but you haven't told Julian yet." He answered causing Brooke to look at him with her mouth open in disbelief.


	6. Author's Note

**Authors Note:**

Hey guys sorry about not updating my story in awhile just been crazy busy but I've finally got back to it, so once I get the chapter the way I want it I will post it. And thank you all for waiting for and reading my story. And thanks to those of you who taken the time to write a review =) I will not leave you guys hanging for much longer, you will just have to wait until after Christmas.

Merry Christmas and Happy New Year to all of you.


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